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Search for "methodology" in Full Text gives 1010 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Transition-state aromaticity and its relationship with reactivity in pericyclic reactions
Beilstein J. Org. Chem. 2025, 21, 1613–1626, doi:10.3762/bjoc.21.125
- that the gain in (in-plane) aromaticity in the parent reaction is not translated into a gain in stability (i.e., a more aromatic transition structure does not translate into a lower-barrier process). Following the same methodology, the ASM of reactivity was applied then to understand the reasons behind
Facile synthesis of hydantoin/1,2,4-oxadiazoline spiro-compounds via 1,3-dipolar cycloaddition of nitrile oxides to 5-iminohydantoins
Beilstein J. Org. Chem. 2025, 21, 1552–1560, doi:10.3762/bjoc.21.118
- regioselectively for both methods. In most cases, the reactions proceeded with high yield and without the formation of significant byproducts. Results and Discussion Synthesis Hydantoins 2, containing an exocyclic C=N group, were synthesized according to the methodology described in [22] (Scheme 1). In brief, N,N
- of nitrile oxides to isocyanates or their dimerization [26][27]. Since isomerization is believed to be the primary direction of molecule degradation only for bulky o,o'-disubstituted aromatic dipoles [28][29][30], the main efforts in developing a methodology were focused on suppressing dimerization
Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions
Beilstein J. Org. Chem. 2025, 21, 1544–1551, doi:10.3762/bjoc.21.117
- and atom-economical strategies for efficiently assembling new carbon–carbon [1][2][3] and carbon–heteroatom [4][5][6] bonds. Thus, it has become the most attractive and facile methodology for creating various complex organic molecular structures from the laboratory to the industrial scale. Among these
Ambident reactivity of enolizable 5-mercapto-1H-tetrazoles in trapping reactions with in situ-generated thiocarbonyl S-methanides derived from sterically crowded cycloaliphatic thioketones
Beilstein J. Org. Chem. 2025, 21, 1508–1519, doi:10.3762/bjoc.21.113
- -established methodology, transient thiocarbonyl S-methanides 1 should be generated in situ by thermal decomposition of their precursors, i.e., spiro-1,3,4-thiadiazolines 2 [5][6]. In contrast to adamantanethione (7a), which reacts with diazomethane (CH2N2) yielding a mixture of regioisomeric 1,3,4- and 1,2,3
Photoredox-catalyzed arylation of isonitriles by diaryliodonium salts towards benzamides
Beilstein J. Org. Chem. 2025, 21, 1480–1488, doi:10.3762/bjoc.21.110
- . Control experiments, Figure S20). Conclusion In conclusion, a novel synthetic methodology for the preparation of benzamides from isonitriles and diaryliodonium salts has been proposed utilizing visible-light photoredox ruthenium-based catalysis. Both symmetrical and unsymmetrical diaryliodonium salts were
Advances in nitrogen-containing helicenes: synthesis, chiroptical properties, and optoelectronic applications
Beilstein J. Org. Chem. 2025, 21, 1422–1453, doi:10.3762/bjoc.21.106
Oxetanes: formation, reactivity and total syntheses of natural products
Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101
- methods for oxetane synthesis, mainly due to its practicality and versatility. 1.1.1.1 Substitution of a leaving group: In 2017, Moody et al. developed a new route towards spiro-oxetanes 8 utilising a combination of 1,4-C–H insertion and Williamson etherification (Scheme 3) [38]. The methodology commences
- oxidation of the metal centre turns the cobalt into an excellent leaving group, allowing for an intramolecular displacement reaction that affords the oxetane ring and regenerates the Co(II) catalyst. In 2023, Silvi et al. described a versatile and practical methodology that couples Williamson etherification
- vinylsulphonium triflates 28 which combine the features of a radical acceptor (in a Giese-type addition) and a leaving group. The use of ketyl radicals for oxetane synthesis was also investigated by Schindler and co-workers and a year later the group published a methodology that utilises a similar Giese addition
Recent advances in amidyl radical-mediated photocatalytic direct intermolecular hydrogen atom transfer
Beilstein J. Org. Chem. 2025, 21, 1306–1323, doi:10.3762/bjoc.21.100
- demonstrated a decent methodology of organic synthesis. These elegant strategies presented powerful C–H bond transformation toolkits (Figure 1b) [6][7][8]. One of the exceptions to the perfection is the pre-functionalization of substrates. Current catalytic methodologies predominantly rely on substrate
- concurrent generation of byproduct 46. Subsequent trapping of radical 4 by HRP-9 leads to the generation of product 69. This methodology demonstrates a broad substrate scope and exhibits significant synthetic utility, particularly for the generation of products 70, 71, and 72 with yields ranging from 54% to
- effectively abstracts a hydrogen atom from the polyolefin substrate, demonstrating notable regioselectivity. The xanthylation reaction preferentially generates main products 76, and byproducts (77 and 78). Furthermore, the successful implementation of this methodology facilitates the production of a diverse
Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents
Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98
- subsequently adds to the activated alkene of N-arylacrylamide, followed by intramolecular cyclization, ultimately leading to the formation of the hydroxy-containing oxindole via the loss of a hydrogen radical. In 2016, Han and colleagues developed a novel methodology in which TBHP served dual roles as both
- ) [6]. This methodology enabled the selective functionalization of one or two C(sp3)–H bonds adjacent to the nitrile group, leading to the formation of diverse polycycles with high selectivity. Various reaction parameters were systematically examined, including Lewis acids, oxidants, bases, reaction
- ions, making a significant contribution to synthetic methodology (Scheme 19) [12]. This method was conducted in an undivided cell, using N-methyl-N-phenylacrylamide 1 and sodium trifluoromethanesulfinate (36) as model reactants. Through meticulous optimization of conditions, including catalyst
Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C–H activation with directing groups
Beilstein J. Org. Chem. 2025, 21, 1171–1182, doi:10.3762/bjoc.21.94
- metallation deprotonation mechanisms mediated by common catalysts like Pd(OAc)2. Our methodology not only identifies potential activation sites but also addresses the limitations of existing models by including a broader range of directing groups and reaction conditions while maintaining moderate
- . Computational Methodology of the QM Workflow The here developed predictive QM-based model calculates which potential reaction site is most likely to react based on its corresponding reaction energy. Following the BEP principle, the relative energy of the intermediate should correlate linearly with the energy of
- groups, we use a different approach to identify relevant palladacycle complexes as in points 1. and 2. outlined in the section “Computational Methodology of the QM Workflow”. Instead of using SMARTS patterns to detect pairs of ortho-directing groups and reaction sites, we detect all potential reaction
Investigations of amination reactions on an antimalarial 1,2,4-triazolo[4,3-a]pyrazine scaffold
Beilstein J. Org. Chem. 2025, 21, 1126–1134, doi:10.3762/bjoc.21.90
- good yield with this straightforward methodology (and without the need for toluene reflux), and to determine the distribution of products obtained for this synthetic approach, by exhaustive analysis of reaction mixtures by HPLC, MS and NMR. Ultimately, 14 aminated derivatives of 5-chloro-3-(4
Synthesis of pyrrolo[3,2-d]pyrimidine-2,4(3H)-diones by domino C–N coupling/hydroamination reactions
Beilstein J. Org. Chem. 2025, 21, 1010–1017, doi:10.3762/bjoc.21.82
- leukaemia, and TAK-285 (H) is a promising HER2/EGFR inhibitor which has been tested in a phase 1 trial on humans as an anticancer agent (Figure 1) [16]. Given the significance of deazapurines as biologically active lead compounds [22], we developed a new methodology for the synthesis of uracil-based
- pyrrolopyrimidine derivatives. The envisioned methodology combines a Sonogashira–Hagihara reaction and a one-pot process comprising a Buchwald–Hartwig coupling reaction followed by a hydroamination [23][24]. Results and Discussion The bromination of 6-chloro-1,3-dimethyluracil (1) afforded, following a known
- groups of those compounds. In contrast, compounds 4a and 4m showed only weak fluorescence with quantum yields of 9 and 4%, respectively. Compound 4j exhibited almost no emission (Φ = 0.1%). [30]. Conclusion In summary, we developed a new methodology for the synthesis of pyrrolo[3,2-d]pyrimidine-2,4(3H
Study of tribenzo[b,d,f]azepine as donor in D–A photocatalysts
Beilstein J. Org. Chem. 2025, 21, 935–944, doi:10.3762/bjoc.21.76
- showed a better performance in comparison with the D–A–D compound 3 (Table 3, entry 7). Furthermore, we obtained pleasing outcomes when we tried the photocatalyzed reductive pinacol coupling of benzaldehyde (15), as reported by Rueping [38]. In this methodology, the reduction of compound 15 is
Silver(I) triflate-catalyzed post-Ugi synthesis of pyrazolodiazepines
Beilstein J. Org. Chem. 2025, 21, 915–925, doi:10.3762/bjoc.21.74
- pyrazolodiazepines 16w and 16x, respectively. Such an outcome is notable, as related carbocyclizations often switch to an exo mode when shifting from internal to terminal alkynes [61][62][63]. To demonstrate the robustness of our methodology, we tested a telescope procedure in which, after the Ugi step, the product
- of post-Ugi transformations leading to the formation of fused seven-membered heterocycles. A series of target pyrazolodiazepines were generated through the variation of substitution patterns on all components of the Ugi reaction while several limitations of the methodology were also identified. In
Recent advances in controllable/divergent synthesis
Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73
- hydrogen atom transfer (HAT)/chiral copper dual catalytic system that achieved regiodivergent and enantioselective C(sp3)–C(sp3) and C(sp3)–N oxidative cross-couplings between N-arylglycine ester/amide derivatives and abundant hydrocarbon C(sp3)–H feedstocks (Scheme 6) [24]. This methodology also
- reduced electrophilicity of the ester carbonyl. In 2021, Dong and Xie reported the development of an azido Matteson reaction, which achieves carbene insertion into an N–B bond of aminoboranes 84 or 86 (Scheme 22) [53]. In this methodology, by controlling the carbene leaving group (alkyl chlorides/alkyl
- (such as indole substrates), Int-79 is more stable at −78 °C, favoring the formation of the mono-insertion product 86. In 2022, Wu and colleagues reported a novel methodology for constructing α-ketoamides 90 or 92 and amides 91 through copper-catalyzed dicarbonylation and monocarbonylation reactions
Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes
Beilstein J. Org. Chem. 2025, 21, 877–883, doi:10.3762/bjoc.21.71
- ). We have studied this reaction and now report a catalytic methodology for the diastereoselective synthesis of these dimeric structures. The high degree of functionalization present in these molecules, which feature two ester groups, an aliphatic gem-dichloride and a dichloroalkene unit, offers ample
Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers
Beilstein J. Org. Chem. 2025, 21, 800–806, doi:10.3762/bjoc.21.63
- by the regio- and stereoselective allylation with p-toluenesulfonyl cyanide. The proposed methodology is efficient for accessing acyclic β,γ-unsaturated nitriles with α-all-carbon quaternary centers and achieves yields up to 99% and excellent regio- and E-selectivity. The reaction proceeds under mild
New advances in asymmetric organocatalysis II
Beilstein J. Org. Chem. 2025, 21, 766–769, doi:10.3762/bjoc.21.60
- -catalyzed reactions and biocatalysis. In the past 25 years, organocatalysis has grown rapidly into a broad area of research, with industrial applications now being developed [16]. The usefulness of any idea or methodology is ultimately often measured by its applications. The robustness, reliability, as well
Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex
Beilstein J. Org. Chem. 2025, 21, 659–669, doi:10.3762/bjoc.21.52
- as trifluorovaline and trifluoroisoleucine were synthesized on a gram‑scale with excellent enantiomeric purities. In this work, we increase the scope of this methodology even further. First, we present the synthesis of two fluorinated, aromatic amino acids: (2,3,5,6)-tetrafluoro-4
Recent advances in allylation of chiral secondary alkylcopper species
Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51
- Abstract The transition-metal-catalyzed asymmetric allylic substitution represents a pivotal methodology in organic synthesis, providing remarkable versatility for complex molecule construction. Particularly, the generation and utilization of chiral secondary alkylcopper species have received considerable
- secondary organocopper; copper-mediated reaction; stereoselectivity; Introduction The transition-metal-catalyzed regio- and enantioselective allylic substitution represents a pivotal methodology in organic synthesis, providing remarkable versatility for complex molecule construction [1][2][3][4]. The
- dialkylzinc reagents as nucleophiles [26]. They subsequently expanded the methodology by successfully employing triorganoaluminum reagents [27]. Recent developments in transition-metal-catalyzed AAA have increasingly turned to organoboron compounds [28][29][30][31]. These reagents offer numerous advantages
Formaldehyde surrogates in multicomponent reactions
Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45
- traps the sulfonium ylide (Scheme 16). In an independent work, Mhaske et al. proposed an alternative methodology to furnish β-amino ketone 20a (Scheme 17), using DMSO as a formaldehyde surrogate but with activation via ammonium persulfate (APS), avoiding the use of transition-metal catalysis [51]. In
- amine with two methyl groups and a benzyl or allyl group, the cleavage of the N–CH2Ph and N–allyl bond takes place more selective (by 85% and 67%, respectively), instead of the cleavage of an N–Me bond. This explains the high selectivity observed for some examples in Scheme 27. Finally, this methodology
- source of formaldehyde but not for ammonia, so the methodology can be used with other amines, too (Scheme 29). Glyoxylate derivatives Due to its low toxicity and reactivity, glyoxylic acid and its glyoxylate derivatives are among the most interesting formaldehyde surrogates in multicomponent reactions
Vinylogous functionalization of 4-alkylidene-5-aminopyrazoles with methyl trifluoropyruvates
Beilstein J. Org. Chem. 2025, 21, 533–540, doi:10.3762/bjoc.21.41
- . Several homoallylic trifluoromethyl carbinols functionalized with a pyrazole moiety were obtained under mild reaction conditions (27–80% yield). This methodology provides a straightforward access to an unprecedented class of trifluoromethyl carbinol derivatives offering a new synthetic approach to
Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction
Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34
- organometallic catalysis [15], enzymatic catalysis [16], aminocatalysis [17][18][19], and hydrogen-bonding catalysis [20][21][22]. The Michael addition reaction is a versatile synthetic methodology that allows the formation of new carbon–carbon and carbon–heteroatom bonds through the coupling of electron-poor
Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions
Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33
- light and promote mass transfer. As understanding of the methodology advances, the development of more complex synthetic strategies, including C–H, C–C, and C–heteroatom-bond formation, is expected [79]. Moreover, we anticipate that the difference in photophysical properties between organic molecules in
Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones
Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26
- antibacterial [4] and cytotoxic activity [6][7]. Existing approaches to the synthesis of 1,3-tropolone derivatives have a number of drawbacks, namely, limited synthesis methodology and low yields of the target compounds [8][9][10][11][12][13][14][15]. Over the past decade, only a few reports have been published
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